Are you interviewing? Or just asking questions.
When you write for a living, you learn pretty quickly that asking good interview questions is more method than instinct.
It’s easy to assume a great interview comes down to chemistry or personality, and it certainly helps. But the real difference is knowing how to ask questions that actually get people past the polished, rehearsed version of what they planned to say.
It starts with specificity. Broad questions get broad answers. If I ask, “What are you seeing?” I’m probably going to get a safe, generic response. But if I ask, “When did you first realize this was changing?” or “What did customers start asking for that they were not asking a year ago?” now we are getting somewhere.
An interview should also feel like a running conversation. The best back-and-forth happens when people recognize you understand their world well enough to ask something beyond the obvious. That means doing enough homework to speak their language at a basic level, to recognize what actually matters in their area of expertise, and to ask follow-up questions that tell them they do not have to start at square one. When they know you know, they stop giving you the basic introductory version. Instead, you get to where the most useful insight lives.
I also think a lot about sequence. You cannot ask people to do four things at once: remember, analyze, summarize and sound smart. Answers will only flatten out, so I try to break it apart: “What changed first?” “What did that affect?” “When did it become clear this was not temporary?” One question at a time, digging deeper with each.
In fact, the best questions are often the simplest follow-ups: “Can you be more specific?” “What did that look like in practice?” “Can you give me an example?” That is usually where the real material shows up—when people tell stories. Stories come with color and character, and that makes content authentic. You get texture, emotion and the small cues that make someone’s perspective worth knowing.
I’ve also come to know that people do not always need tougher questions, but room for honesty. Because if you only ask about success, you are probably going to get the clean, sterile version they have told before. But if you ask, “What went wrong at first?” or “What ended up being harder than you expected?” or “Where did the plan break down?” that is usually when things get interesting. And those answers are almost always more useful.
I think good interviewing is equal parts curiosity, discipline and engagement. You go in prepared, with a point of view, ready to listen and eager to explore the real story that is always lurking just beneath the surface.
The goal is never just to get someone talking. It’s to get to something worth saying.
Want to learn more about what we're talking about and ensure your subject matter experts are being given the chance to tell their story? Email ben.brugler@akhia.com
Thanks for reading!